In ancient times, travelers who were on their way to Rome after leaving Siena had two options in front of them: continue along the Via Cassia or choose the Via Lauretana.

By following the Via Cassia, travelers went through what is now known as the Val d’Orcia: San Quirico, Montalcino and Pienza. These are unmissable stops for lovers of Brunello wine, Pecorino cheese and those who want to see the “ideal city” from the Renaissance era. Pienza was built at the behest of Pope Pius II, thanks to the wisdom of the architect Bernardo Rossellino, and was one of the first examples of city planning.

The Val d’Orcia gives way to the Val di Chiana right near the town of Montepulciano: a splendid medieval city known for its production of Nobile di Montepulciano wine. The ancient Etruscans, who moved from Siena towards the Arezzo area, crossed the Via Lauretana (the ancient road that connected Siena to Cortona) passing through what are now known as the Crete Senesi before reaching Montepulciano.